Chincoteague Rentals - Flex Stay Homes

Here at Seaside Vacations, we understand how busy life is, and that you can't always get away for a full week. That's what we LOVE about our Flex Stay Program ~ Arrive when you want, depart when you want, the world is your Oyster (it's a Chincoteague thing)! The homes in our Flex Stay Program have either a 2 or 3 night minimum all year long, not just the Off-Season! As always, we're standing by ready to help you find just the right home for your next Beach Break!

Browse these amazing Chincoteague Rentals with Flexible Stays so you can check-in on your schedule and not by a schedule set for you.

Search and book online today!


Properties Available 71 properties available
Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course
Hot HOT 23
Assateague Inn 103-S
Condominium
$45 - $355 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Life’s a Beach - If you’re not barefoot, you’re overdressed….When was the last time your Vacation made you happier than a Seagull with a french fry? If you’ve been searching for just the right place - or just the right Experience, we should say - boy, do we have the place for you! K and S Paradise is nestled right in the heart of Chincoteague Islan
Hot HOT 19
K and S Paradise
House Pet Friendly
$100 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Memories at the Beach last a lifetime…..Hoping to land the big one this year for your Chincoteague Island Vacation? Look no further than adorable “Catch of the Day” on super quiet and peaceful Tim Lane, just off Deep Hole Road, in the very heart of Chincoteague Island!This delightful Duplex sits tucked at the end of the Lane, surrounded by peaceful
Hot HOT 19
Catch of the Day
Town House
$110 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 guests
Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Ocean Pearl Cottage, but the words comfy, cozy, and charming come to mind. This quintessential Chincoteague Cottage is just a short stroll from Main Street Restaurants, Shops, and Robert Reed Waterfront Park - home to THE most ama
Hot HOT 19
Ocean Pearl Cottage
House Pet Friendly
$95 - $250 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 6 guests
Sky above, Sand below, Peace within…..Here at Seaside, we believe that finding the “perfect” Vacation Home is so much more than merely finding a place to lay your head at night. We are all about “Experiences” ~ and a stay at ‘East Side Breezes’ is just that ~ a blissful Experience that will be treasured by your family for years to come. This specta
Hot HOT 13
East Side Breezes
House
$125 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course
Hot HOT 14
Assateague Inn 208-S
Condominium
$45 - $363 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Collect Memories, not things…..Life is busy - crazy busy! Work, school, meetings, sports - and repeat. Precious moments together that used to be easy to find, are hard to come by these days. This is why we must MAKE them happen! So, clear the calendar and grab those who matter most - we’ve got the Vacation of a lifetime for you right here on Chinco
Hot HOT 216
Teal Cottage
House
$150 - $500 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Bella Vista - Everything is better with a Water View…..Welcome to Sunset Bay 319 - Bella Vista - at fabulous Sunset Bay Villas on the Chincoteague Bay. Bella Vista, which is Italian for ‘beautiful View’, more than lives up to its name with stunning Direct Bayfront Views all around. These gorgeous condos sit directly on the Bay with spectacular View
Hot HOT 21
Sunset Bay Villa 319 - Bella Vista
Condominium
$150 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Deja Blue - there is no color quite like this…..You know that feeling when you see the Ocean and all your worries just wash away? That’s the feeling you get as soon as you walk through the French Doors at Deja Blue on Chincoteague Island. This adorable Cottage oozes that quintessential Chincoteague Charm you love, plus has the Modern Amenities you
Hot HOT 13
Deja Blue
House
$90 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 guests
Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course
Hot HOT 18
Assateague Inn 211-S
Condominium
$45 - $355 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Trees listen to the Breeze; and then rustle its voice so beautifully….Looking for a getaway that makes you feel a million miles from the real world? Just imagine kicking back under the shade of tall Pine Trees - swaying in the breeze, while you listen to the Tree Frogs sing - pure bliss. Whispering Pines is not just a place to lay your head at nigh
Hot HOT 32
Whispering Pines
Town House Pet Friendly
$145 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
The Happy Crab - Where dreams are made of Sun and Sand…..There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the family together can be such a challenge in today's world, but nothing is more important than doing just that. Clear the calendar, grab those you love, and head to Chincoteague I
Hot HOT 19
The Happy Crab
Town House
$120 - $395 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests

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